Reactions of ninhydrin with activated anilines: Formation of indole derivatives
In benzene, ninhydrin undergoes electrophilic substitution at C2 of 3,5-dimethoxyaniline leading to the indeno[1,2-b]indole (7): the corresponding reaction in water undergoes electrophilic substitution at C4 to give compound (11).
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Cited by (44)
Structural, CSD, and computational studies of 6b, 11b-Dihydroxy-6b, 11-b-dihydro-7H-indeno[1,2-b]naptho[2,1-d]furan-7-one, a therapeutic potential small molecule
2021, Journal of Molecular StructureCitation Excerpt :The dihedral angle between the mean plane of the rings A/B/C (plane 1: 13 atoms) and D/E (plane 2: 9 atoms) is 75.94° for the title compound DHFO, showing that a tilt occurs in the plane of the molecule in the region between rings C and D. This phenomenon is ubiquitous and observed in similar structures [8–10,28–34]. For the CSD structures, the dihedral angle between the mean plane for rings B/C, and D/E range from 65.57° (ADAYEL-Mol5) to 80.42° (UNUZOT-Mol2) (Supplementary Table S8), probably because of oxygen atoms in the hydroxyl, as well as the C = O moieties in ADAYEL, are covalently connected to the heavy atom rubidium.
Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9
2015, European Journal of Medicinal ChemistryCitation Excerpt :Recently, two new syntheses by transformation and reduction of 2-nitrobenzylidenephtalide, generated either by intramolecular cyclization of 2-(2-nitrophenylethyl)benzoic acid [26], or by reaction of a phthalidyl-phosphonium bromide with 2-nitrobenzaldehyde [27] and cyclization of the resulting amino compounds, have been published. The formation of vic-dihydroxy-indenoindolones by the reaction of ninhydrine 1 with aliphatic, and aromatic amines, or alicyclic, and cyclic enaminones has been reported elsewhere [28–33]. The intermediates 4 and 5 were achieved according to published procedures by refluxing cyclohexane-1,3-dione with aromatic amine and a catalytic amount of p-toluensulfonic acid in toluene and removal of water as an azeotrope with a Dean–Stark water trap [34].
Efficient synthesis of 3H,3′H-spiro[benzofuran-2,1′- isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition
2013, European Journal of Medicinal ChemistryCitation Excerpt :Lactum form of this spiro substructure is also present in Streptospirole derivatives, derived from microorganism Streptomyces, which are known to inhibit bacterial growth [23]. In spite of this, there are only a few methods available and all of them involve multistep synthesis [24–27]. Moreover, the previous reports available for these 3H,3′H-spiro[benzofuran-2,1′-isobenzofuran]-3,3′-diones A have never attracted interest among the medicinal chemists for its application.
Novel spiro-sesquiterpene from the mushroom Anthracophyllum sp. BCC18695
2013, Phytochemistry LettersCitation Excerpt :The optical rotation of compound 1 ([α]D −28.4200 in MeOH) indicated the presence of its diastereoisomer. The synthesis of spiro oxygen- and nitrogen-containing substances, especially spiro phthalides, was studied for improving the biological properties (Black et al., 1994; Mohammadizadeh et al., 2010). Compound 2 ([α]D27 +146.0933 (c 0.15, MeOH), named as anthracophyllone) gave the mass ion peak at m/z 255.1347 [M+Na]+, suggesting the molecular formula as C15H20O2.